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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-04-06 16:21:47 UTC

Update Date

2022-03-07 02:51:22 UTC

HMDB ID

HMDB0012252

Secondary Accession Numbers

HMDB12252

Metabolite Identification

Common Name

Linoleoyl ethanolamide

Description

Linoleoyl ethanolamide, also known as linoleamide mea or anandamide (18:2, N-6), belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine. Thus, linoleoyl ethanolamide is considered to be a fatty amide. Based on a literature review very few articles have been published on Linoleoyl ethanolamide.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0012252
     RDKit          3D
Linoleoyl ethanolamide
 60 59  0  0  0  0  0  0  0  0999 V2000
   -6.5136    3.1603   -3.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0271    1.9948   -2.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5519    2.1486   -1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684    2.1843   -1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858    0.9302   -1.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7896   -0.2721   -0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0626   -1.0974   -0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6423   -1.1010    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162   -0.0038   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -0.0999   -1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587   -1.3462   -1.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758   -1.6969   -1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530   -1.8602    0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279   -2.2103    0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0212   -2.3966    1.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4815   -2.7367    1.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4174   -1.6981    1.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3075   -0.3751    1.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5096   -0.1566    2.9225 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1247    0.6742    1.5163 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0575    1.9754    2.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4181    1.9166    3.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3310    3.2251    4.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7168    2.7682   -4.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0567    3.9509   -2.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3378    3.5623   -4.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1603    2.0166   -2.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7653    1.0082   -2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9076    1.3007   -0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0312    3.0602   -0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6375    3.0768   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8006    2.3185   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017    0.7837   -2.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435    1.1315   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8885   -0.5062   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6715   -1.9606    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920   -1.1750    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2236   -2.1180   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0150    1.0156    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704    0.8342   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166   -1.1424   -2.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -2.2207   -1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7573   -0.8736   -1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.6649   -1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539   -2.7431    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9682   -0.9433    0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801   -3.1941   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3303   -1.4040   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7630   -1.5282    2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339   -3.2670    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7394   -3.6917    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7181   -2.8765    2.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328   -1.5402    0.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4485   -2.0692    1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7861    0.5134    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0265    2.4134    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7124    2.7004    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4399    1.5104    3.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244    1.3206    4.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6438    3.1849    5.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
M  END


  Mrv1652301171918382D          

 23 22  0  0  0  0            999 V2000
 9981.3167 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.0302 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7458 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.4593 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1749 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.8899 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6046 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.4301 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.1448 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.8596 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.6852 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.3999 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.1147 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.8294 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.5463 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.2612 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.6011 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.8855 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.1720 9984.0396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9978.4564 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.7388 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.0253 9984.4513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9979.8855 9985.2768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012252

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/CCCCCCCC(=O)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C20H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h6-7,9-10,22H,2-5,8,11-19H2,1H3,(H,21,23)/b7-6-,10-9-

> <INCHI_KEY>
KQXDGUVSAAQARU-HZJYTTRNSA-N

> <FORMULA>
C20H37NO2

> <MOLECULAR_WEIGHT>
323.5133

> <EXACT_MASS>
323.282429433

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
41.410886059353125

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide

> <ALOGPS_LOGP>
6.26

> <JCHEM_LOGP>
5.148508234333334

> <ALOGPS_LOGS>
-5.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.47384261938588

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.469626555316175

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3086129187290516

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
101.52999999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.20e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
linoleamide mea

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012252
     RDKit          3D
Linoleoyl ethanolamide
 60 59  0  0  0  0  0  0  0  0999 V2000
   -6.5136    3.1603   -3.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0271    1.9948   -2.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5519    2.1486   -1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684    2.1843   -1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858    0.9302   -1.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7896   -0.2721   -0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0626   -1.0974   -0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6423   -1.1010    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162   -0.0038   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -0.0999   -1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587   -1.3462   -1.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758   -1.6969   -1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530   -1.8602    0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279   -2.2103    0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0212   -2.3966    1.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4815   -2.7367    1.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4174   -1.6981    1.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3075   -0.3751    1.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5096   -0.1566    2.9225 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1247    0.6742    1.5163 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0575    1.9754    2.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4181    1.9166    3.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3310    3.2251    4.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7168    2.7682   -4.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0567    3.9509   -2.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3378    3.5623   -4.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1603    2.0166   -2.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7653    1.0082   -2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9076    1.3007   -0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0312    3.0602   -0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6375    3.0768   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8006    2.3185   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017    0.7837   -2.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435    1.1315   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8885   -0.5062   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6715   -1.9606    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920   -1.1750    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2236   -2.1180   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0150    1.0156    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704    0.8342   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166   -1.1424   -2.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -2.2207   -1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7573   -0.8736   -1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.6649   -1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539   -2.7431    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9682   -0.9433    0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801   -3.1941   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3303   -1.4040   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7630   -1.5282    2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339   -3.2670    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7394   -3.6917    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7181   -2.8765    2.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328   -1.5402    0.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4485   -2.0692    1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7861    0.5134    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0265    2.4134    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7124    2.7004    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4399    1.5104    3.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244    1.3206    4.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6438    3.1849    5.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
M  END

HEADER    PROTEIN                                 17-JAN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JAN-19         0                                  
HETATM    1  C   UNK     0    8631.7918637.642   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8633.1238636.874   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8634.4598637.642   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8635.7918636.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8637.1268637.642   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8638.4618636.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8639.7958637.642   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8641.3368637.642   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8642.6708636.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8644.0058637.642   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8645.5468637.642   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8646.8808636.874   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8648.2148637.642   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8649.5488636.874   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8650.8868637.642   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8652.2218636.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8630.4558636.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8629.1208637.642   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0    8627.7888636.874   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0    8626.4528637.642   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8625.1128636.874   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8623.7818637.642   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0    8629.1208639.183   0.000  0.00  0.00           O+0
CONECT    1    2   17                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17    1   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0012252
HETATM    1  C1  UNL     1      -6.514   3.160  -3.408  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.027   1.995  -2.593  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.552   2.149  -1.167  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.068   2.184  -1.084  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.386   0.930  -1.625  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.790  -0.272  -0.926  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.063  -1.097  -0.235  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.642  -1.101   0.072  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.816  -0.004  -0.377  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.804  -0.100  -1.219  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.359  -1.346  -1.835  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.076  -1.697  -1.485  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.253  -1.860   0.011  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.728  -2.210   0.227  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.021  -2.397   1.701  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.482  -2.737   1.845  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.417  -1.698   1.318  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.308  -0.375   1.973  1.00  0.00           C  
HETATM   19  O1  UNL     1       4.510  -0.157   2.922  1.00  0.00           O  
HETATM   20  N1  UNL     1       6.125   0.674   1.516  1.00  0.00           N  
HETATM   21  C19 UNL     1       6.057   1.975   2.118  1.00  0.00           C  
HETATM   22  C20 UNL     1       6.418   1.917   3.579  1.00  0.00           C  
HETATM   23  O2  UNL     1       6.331   3.225   4.098  1.00  0.00           O  
HETATM   24  H1  UNL     1      -5.717   2.768  -4.099  1.00  0.00           H  
HETATM   25  H2  UNL     1      -6.057   3.951  -2.780  1.00  0.00           H  
HETATM   26  H3  UNL     1      -7.338   3.562  -4.029  1.00  0.00           H  
HETATM   27  H4  UNL     1      -8.160   2.017  -2.617  1.00  0.00           H  
HETATM   28  H5  UNL     1      -6.765   1.008  -2.998  1.00  0.00           H  
HETATM   29  H6  UNL     1      -6.908   1.301  -0.541  1.00  0.00           H  
HETATM   30  H7  UNL     1      -7.031   3.060  -0.733  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.637   3.077  -1.594  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.801   2.319  -0.004  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.802   0.784  -2.704  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.343   1.131  -1.755  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.888  -0.506  -1.002  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.671  -1.961   0.195  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.492  -1.175   1.221  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.224  -2.118  -0.228  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.015   1.016   0.041  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.270   0.834  -1.462  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.317  -1.142  -2.958  1.00  0.00           H  
HETATM   42  H19 UNL     1      -0.981  -2.221  -1.738  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.757  -0.874  -1.799  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.354  -2.665  -1.948  1.00  0.00           H  
HETATM   45  H22 UNL     1       0.654  -2.743   0.366  1.00  0.00           H  
HETATM   46  H23 UNL     1       0.968  -0.943   0.567  1.00  0.00           H  
HETATM   47  H24 UNL     1       2.880  -3.194  -0.262  1.00  0.00           H  
HETATM   48  H25 UNL     1       3.330  -1.404  -0.188  1.00  0.00           H  
HETATM   49  H26 UNL     1       2.763  -1.528   2.324  1.00  0.00           H  
HETATM   50  H27 UNL     1       2.434  -3.267   2.083  1.00  0.00           H  
HETATM   51  H28 UNL     1       4.739  -3.692   1.333  1.00  0.00           H  
HETATM   52  H29 UNL     1       4.718  -2.876   2.929  1.00  0.00           H  
HETATM   53  H30 UNL     1       5.333  -1.540   0.229  1.00  0.00           H  
HETATM   54  H31 UNL     1       6.449  -2.069   1.496  1.00  0.00           H  
HETATM   55  H32 UNL     1       6.786   0.513   0.736  1.00  0.00           H  
HETATM   56  H33 UNL     1       5.026   2.413   1.994  1.00  0.00           H  
HETATM   57  H34 UNL     1       6.712   2.700   1.572  1.00  0.00           H  
HETATM   58  H35 UNL     1       7.440   1.510   3.697  1.00  0.00           H  
HETATM   59  H36 UNL     1       5.724   1.321   4.192  1.00  0.00           H  
HETATM   60  H37 UNL     1       6.644   3.185   5.033  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    7   35
CONECT    7    8   36
CONECT    8    9   37   38
CONECT    9   10   10   39
CONECT   10   11   40
CONECT   11   12   41   42
CONECT   12   13   43   44
CONECT   13   14   45   46
CONECT   14   15   47   48
CONECT   15   16   49   50
CONECT   16   17   51   52
CONECT   17   18   53   54
CONECT   18   19   19   20
CONECT   20   21   55
CONECT   21   22   56   57
CONECT   22   23   58   59
CONECT   23   60
END

HMDB0012252
     RDKit          3D
Linoleoyl ethanolamide
 60 59  0  0  0  0  0  0  0  0999 V2000
   -6.5136    3.1603   -3.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0271    1.9948   -2.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5519    2.1486   -1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684    2.1843   -1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858    0.9302   -1.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7896   -0.2721   -0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0626   -1.0974   -0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6423   -1.1010    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162   -0.0038   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -0.0999   -1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587   -1.3462   -1.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758   -1.6969   -1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530   -1.8602    0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279   -2.2103    0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0212   -2.3966    1.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4815   -2.7367    1.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4174   -1.6981    1.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3075   -0.3751    1.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5096   -0.1566    2.9225 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1247    0.6742    1.5163 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0575    1.9754    2.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4181    1.9166    3.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3310    3.2251    4.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7168    2.7682   -4.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0567    3.9509   -2.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3378    3.5623   -4.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1603    2.0166   -2.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7653    1.0082   -2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9076    1.3007   -0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0312    3.0602   -0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6375    3.0768   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8006    2.3185   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017    0.7837   -2.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435    1.1315   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8885   -0.5062   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6715   -1.9606    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920   -1.1750    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2236   -2.1180   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0150    1.0156    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704    0.8342   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166   -1.1424   -2.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -2.2207   -1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7573   -0.8736   -1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.6649   -1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539   -2.7431    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9682   -0.9433    0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801   -3.1941   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3303   -1.4040   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7630   -1.5282    2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339   -3.2670    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7394   -3.6917    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7181   -2.8765    2.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328   -1.5402    0.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4485   -2.0692    1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7861    0.5134    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0265    2.4134    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7124    2.7004    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4399    1.5104    3.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244    1.3206    4.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6438    3.1849    5.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9Z,12Z)-N-(2-Hydroxyethyl)octadeca-9,12-dien-1-amide	ChEBI
Anandamide (18:2, N-6)	ChEBI
Linoleamide mea	ChEBI
Linoleic ethanolamide	ChEBI
Linoleoyl monoethanolamide	ChEBI
Monoethanolamine linoleic acid amide	ChEBI
N-(2-Hydroxyethyl)-9,12-octadecadienamide	ChEBI
N-(2-Hydroxyethyl)linoleamide	ChEBI
N-(9Z,12Z-Octadecadienoyl)-ethanolamine	ChEBI
N-cis-9-cis-12-Octadecadienoylethanolamine	ChEBI
Monoethanolamine linoleate amide	Generator
LEA	HMDB
N-(2-Hydroxyethyl)-linoleamide	HMDB
Linoleoylethanolamide	HMDB
Linoleoyl ethanolamide	MeSH

Chemical Formula

C₂₀H₃₇NO₂

Average Molecular Weight

323.5133

Monoisotopic Molecular Weight

323.282429433

IUPAC Name

(9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide

Traditional Name

linoleamide mea

CAS Registry Number

68171-52-8

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(=O)NCCO

InChI Identifier

InChI=1S/C20H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h6-7,9-10,22H,2-5,8,11-19H2,1H3,(H,21,23)/b7-6-,10-9-

InChI Key

KQXDGUVSAAQARU-HZJYTTRNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

N-acylethanolamines

Alternative Parents

Substituents

N-acylethanolamine
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-(polyunsaturated fatty acyl)ethanolamine (CHEBI:64032 )
N-(long-chain-acyl)ethanolamine (CHEBI:64032 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040004 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)
Urine (PMID: 32966057)

Cellular substructure

Extracellular (HMDB: HMDB0012252)
Membrane (HMDB: HMDB0012252)

Source

Exogenous

Exogenous (HMDB: HMDB0012252)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0012252)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	499.06 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.11 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.003 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00042 g/L	ALOGPS
logP	6.26	ALOGPS
logP	5.15	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	15.47	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	101.53 m³·mol⁻¹	ChemAxon
Polarizability	41.41 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	188.818	31661259
DarkChem	[M-H]-	187.886	31661259
DeepCCS	[M+H]+	191.387	30932474
DeepCCS	[M-H]-	189.029	30932474
DeepCCS	[M-2H]-	221.916	30932474
DeepCCS	[M+Na]+	197.48	30932474
AllCCS	[M+H]+	188.2	32859911
AllCCS	[M+H-H2O]+	185.5	32859911
AllCCS	[M+NH4]+	190.7	32859911
AllCCS	[M+Na]+	191.4	32859911
AllCCS	[M-H]-	187.0	32859911
AllCCS	[M+Na-2H]-	189.0	32859911
AllCCS	[M+HCOO]-	191.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.18 minutes	32390414
Predicted by Siyang on May 30, 2022	20.6152 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.12 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2993.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	388.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	212.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	231.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	633.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	927.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	633.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	160.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1956.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	642.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1815.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	677.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	486.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	384.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	423.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.6 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Linoleoyl ethanolamide,1TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C	2698.3	Semi standard non polar	33892256
Linoleoyl ethanolamide,1TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C	2602.1	Standard non polar	33892256
Linoleoyl ethanolamide,1TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C	2974.0	Standard polar	33892256
Linoleoyl ethanolamide,1TMS,isomer #2	CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C	2653.3	Semi standard non polar	33892256
Linoleoyl ethanolamide,1TMS,isomer #2	CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C	2596.7	Standard non polar	33892256
Linoleoyl ethanolamide,1TMS,isomer #2	CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C	3046.2	Standard polar	33892256
Linoleoyl ethanolamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2690.3	Semi standard non polar	33892256
Linoleoyl ethanolamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2738.0	Standard non polar	33892256
Linoleoyl ethanolamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2781.4	Standard polar	33892256
Linoleoyl ethanolamide,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C	2929.7	Semi standard non polar	33892256
Linoleoyl ethanolamide,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C	2783.9	Standard non polar	33892256
Linoleoyl ethanolamide,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C	3005.2	Standard polar	33892256
Linoleoyl ethanolamide,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	2871.2	Semi standard non polar	33892256
Linoleoyl ethanolamide,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	2801.7	Standard non polar	33892256
Linoleoyl ethanolamide,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	3068.3	Standard polar	33892256
Linoleoyl ethanolamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3165.2	Semi standard non polar	33892256
Linoleoyl ethanolamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3072.8	Standard non polar	33892256
Linoleoyl ethanolamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2879.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Linoleoyl ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0jbd-6980000000-296b477e994954e1473b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linoleoyl ethanolamide GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9543000000-ffd6c325474236c1ad72	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linoleoyl ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 10V, Positive-QTOF	splash10-0229-6149000000-bb2fbbe45488da8f67b4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 20V, Positive-QTOF	splash10-03dl-9120000000-186b72964c13d07734a1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 40V, Positive-QTOF	splash10-03dl-9310000000-74ec109576a7e198699a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 10V, Negative-QTOF	splash10-00di-0029000000-cbc91ff6d8043670d9ba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 20V, Negative-QTOF	splash10-0h93-8079000000-a00a0ae3a1220d221577	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 40V, Negative-QTOF	splash10-0006-9010000000-2aa2259713b6e2b19532	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 10V, Negative-QTOF	splash10-00di-0009000000-136b1b8ae59ab6324a70	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 20V, Negative-QTOF	splash10-00di-5139000000-5a2a20a7ee6a618f5798	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 40V, Negative-QTOF	splash10-06r6-9010000000-f671867a64400c3cd77c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 10V, Positive-QTOF	splash10-0229-9117000000-85c2fb6d17d62e45e299	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 20V, Positive-QTOF	splash10-03dl-9000000000-b5bb3da43d166e8e9d05	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linoleoyl ethanolamide 40V, Positive-QTOF	splash10-07bf-9000000000-49357c837f95951f6615	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	13.7 +/- 6.5 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028893

KNApSAcK ID

Not Available

Chemspider ID

4446566

KEGG Compound ID

Not Available

BioCyc ID

CPD6666-4

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283446

PDB ID

Not Available

ChEBI ID

64032

Food Biomarker Ontology

Not Available

VMH ID

LINETH

MarkerDB ID

Not Available

Good Scents ID

rw1301201

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Linoleoyl ethanolamide (HMDB0012252)

MOL for HMDB0012252 (Linoleoyl ethanolamide)

3D MOL for HMDB0012252 (Linoleoyl ethanolamide)

3D SDF for HMDB0012252 (Linoleoyl ethanolamide)

3D-SDF for HMDB0012252 (Linoleoyl ethanolamide)

PDB for HMDB0012252 (Linoleoyl ethanolamide)

3D PDB for HMDB0012252 (Linoleoyl ethanolamide)

SMILES for HMDB0012252 (Linoleoyl ethanolamide)

INCHI for HMDB0012252 (Linoleoyl ethanolamide)

Structure for HMDB0012252 (Linoleoyl ethanolamide)

3D Structure for HMDB0012252 (Linoleoyl ethanolamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra